iCloud Round 2: Outlook Sync Improved in iCloud 2.0


iCloud Redeemed?Trouble in Paradise

Several weeks ago, I got fed up with the problems of iCloud syncing with Outlook and made the decision to switch to syncing with Microsoft Exchange. Initially, this seemed to be working out well, but I later realized that my contacts’ birthdays kept migrating to different days. Some were one day off; many were several days off.

There were some other small issues with Exchange sync on iOS–tasks didn’t sync at all, you couldn’t have contact groups, and certain contact fields in iOS were not supported, such as related people. But the birthday bug was the deal-breaker for me.

I did some research on this and what I learned is that it was a bug introduced by Microsoft which was copied into Apple’s code for Exchange sync. It was later fixed in Microsoft’s Outlook Connector for Hotmail, but Apple had never corrected the buggy code on their end–even though it has been known for more than two years.

Searching for a Sync Solution

So, I went about the task of looking for yet another Outlook <-> iOS sync solution, even if I had to pay for it. I came across Fruux, which looked promising, but then I learned that they do not yet support Outlook sync. According to a Twitter conversation I had with them, it’s something they are working on. So, I will be keeping an eye on that.

I found a lot of great information on the Slipstick Systems website, and this is where I learned that several of the Outlook compatibility issues were resolved in the iCloud Control Panel version 2. I also found out about CodeTwo Sync for iCloud which enables you to keep your standard Outlook folders in sync with your iCloud folders in Outlook. The CodeTwo sync tool is worth looking into if you need to stay on iCloud 1.0 for some reason, but if you use iCloud 2.0, it is not necessary.

I also briefly investigated eM Client, an Outlook replacement, which advertises iOS syncing. I got as far as installing it, but decided I wasn’t ready to change my email client and learn a whole new PIM program. Plus, I learned that eM Client relies on Microsoft Exchange for sync and I was afraid it would result in the same birthday problem I was trying to resolve.

iCloud Round 2

Deep breath time… Am I really considering going back to iCloud? Yes, that is what I did.

I spent a day fixing my contacts’ birthdays, and (again) merging my contacts, calendar, and tasks back into one unified Outlook data file. I also deleted everything from iCloud–both in the cloud (icloud.com) and on my iOS devices. Then, with iCloud 2 installed, I once again enabled Contacts, Calendar, and Reminders sync for iCloud. This time, iCloud automatically changed the default data file in Outlook to be iCloud, and… it is working!

iCloud as Outlook data File

iCloud becomes the default data file in iCloud 2.0.

I have been doing a lot of testing with editing and syncing, and for the most part it is working very well. My newly created items in Outlook now go to the iCloud data file by default and I do not have to remember to move them to get them on my iDevices. Event and Tasks reminders no longer trigger two popup windows on my desktop, and they can be snoozed. I have not seen calendar events moving, but it will take some time to determine if this is truly improved.

iCloud 2.0 Caveats

There are still a few things that don’t work perfectly when syncing Outlook with iCloud 2.0:

  • When a task reminder pops up in Outlook, you can’t right click to mark it complete. You also can’t double-click to open it. You have to find it in your tasks list to mark it completed. Or you can mark it completed in iOS and it will transfer the completed status back to Outlook.
  • New tasks do not appear in the To-Do bar in the desktop Outlook. Only tasks that were created prior to enabling iCloud sync are shown in the To-Do bar.
  • You can’t send email from IMAP email accounts in Outlook. If you use IMAP accounts, you will need to switch them to POP3 in Outlook in order to send mail.

After two weeks, those are the only problems I have encountered so far. If I run across any new issues, I will add them to this post.

Savi ContactsOne thing that is nice about doing sync this way is that I can have contact groups. I’m not sure if you can create the contact groups in Outlook. I created them using a free app called Savi Contacts on iOS and the groups transferred back to Outlook on my desktop.

As long as the Task/Reminder issues are not a big deal for you, and you don’t need to send email from IMAP accounts in Outlook, I would say it is safe to go back to syncing Outlook with iCloud 2.0. But, I do highly recommend reading everything relating to iCloud on the Slipstick website before making a decision. Of course, if you are not bothered by the birthday bug and lack of Tasks sync using Microsoft Exchange, that is another way to go.


Categories: iOS

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16 Responses to “iCloud Round 2: Outlook Sync Improved in iCloud 2.0”

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  1. Scott says:

    Sue – I’m using iCloud 2, but only for calendar and contacts – not email. Can I still change my default data file to iCloud? If I change the default data file to iCloud, will it mess up anything with my email?

    When someone sends me a calendar invite and I accept, I want it to save the meeting appointment in my iCloud calendar, not my default calendar.



    • Sue says:

      Hi Scott. I don’t use email either and it works fine with iCloud as my default data file. I can’t answer about calendar invites, but if you make iCloud the default it should work.

      • Scott says:

        Well, I tried changing the Outlook default data file from my personal account to iCloud. Unfortunately, it did mess up my email. I’m using Outlook 2007, iCloud 2 and I have a pop 3 account with yahoo email. I could no longer receive or send email. When I tried to compose an email, I received an error message that said “You don’t have permission to create an entry in this folder. Right-click the folder, then click Properties to check your permissions for the folder. See the folder owner or your administrator to change your permissions.” I searched that error message online and was unable to find any solutions. Let me know if you have a suggestion.



  2. Andrew Hayman says:

    Sue – thank you for this – it might solve my problems.
    Like you I can see that i-Tunes is not fit for purpose as a sync-interface for contacts. Also the functionality has been downgraded from ver 10 to ver 11 (no more support for Windows Contacts nor Google Contacts … so all the time spent there was wasted).
    Question: (A) is there a limit on the number of contacts Outlook can handle (I have Outlook 2010) (B) How about the iPhone 4 ? This does not appear to be documented. I have a large contact database … probably too large at 25,000 professional entries (no, I’m not a spammer). But I don’t have the time or inclination to clean it all up. I just want to sync a smaller number – say 5000 – to my iPhone and have CONTACT GROUPS that match on either end. And no horrible mismatches !

  3. Jason Winter says:

    We have tried everything we can think of to get Oultlook 2010 to sync with ICloud 2. We have be syncing calendar, contacts and emails fine for the past year or so, then it just quit working (email syncs fine). We have been on the phone with Microsoft with no avail. Jason

    • Sue says:

      Sorry, Jason. Apparently it is still flaky for a lot of people. I guess you tried all the usual suggestions–signing out and back in, uninstalling and reinstalling all the Apple stuff, removing and reinstalling the Outlook iCloud addin? There are some tips and suggestions on the Slipstick site linked from this article that you might want to check out. I can see this being a frustrating case of Microsoft blaming Apple and Apple blaming Microsoft. :-/ Wish I could offer some insight but it has been working okay for me, knock wood.

  4. Paul says:

    I have a MS Exchange through my work, with Outlook 2010 on my desktop. Can I use iCloud 2 to sync my contacts and calender with my iphone?

    • Sue says:

      I don’t see why not, Paul.

      • Paul says:

        At work we have Windows XP ,so I had to hack iCloud Ver 1 to work with Outlook 2010. I have not tried hacking and installing iCloud V2 yet.

        I have been syncing icloud folders in outlook with the CodeTwo Sync for iCloud. I keep getting contacts shown twice on my exchange folder (ghost images) and in my icloud folder in outlook (but not echoed into icloud actual).

        I may try the folder sync from CodeTwo and see if that helps, since icloud is showing as folders…

  5. Luis Nunes says:

    hello. i also have this issue (of course i do!). I’ve tried the solution pointed in using exchange and almost worked out right. For some reason the sync between outlook and hotmail doesn’t work very fast. Tested creating an appointment in outlook and it just wouldn’t appear in the web server. Sync between hotmail and iphone worked very well. So i read this other post. I already had icloud 2.0 installed but checked to see if any update was available, found one. Icloud 2.1.1. Uninstalled and reinstalled this new one… changed everything back into icloud… nope… doesn’t work, Still doesn’t allow icloud as my default folders and outlook hangs on start. Switching back to the hotmail solution and starting to thinking about my next communication company contract review (later this year..) to put my hands on some other device that just syncs well with outlook. It’s really a shame what greed and business can do (or better saying what stops us from doing…) to our intelligence because iphone is by far the best phone i’ve ever had… but if i can’t use it to have my agenda, contacts, tasks and notes.. wich is one thing i’m used to have on my hands since there was once a device called a PDA … well.. i think i’ll better not have an iphone. Too bad Apple. hope you one day open your eyes and realize that the best way to have a sucessfull business is by having your clients happy with your products and not by forcing them to switch to anything.
    This is the main annoying thing iphone for me, because there are many others.. like the (un)ability to have a simple spreadsheet editable in my hands… wow.. Back in 2000 i had a PDA – ASUS … a big brick on my pocket and it had EXCEL, WORD, POWERPOINT, etc… i could take all my spreadsheets with me.. now.. i can only read them! Unless of course i pay for a basic thing on a 600€+ phone from apple store. Well done! One day in the future, You pay 600€ for a phone but if you want the sync cable.. you pay extra.. if you want it in a box.. you pay extra.. if you want the charger.. you pay extra.
    My operating system is windows 7, Outlook 2007, Iphone 4S (for the meanwhile… but thinking about samsung galaxy siii)

  6. David S. says:

    I am also dealing with issues about synching Outlook calendar and contacts with iCloud. I don’t want to mess with my current personal email account in Outlook because it is working just fine and I have lots of folders for it. So I don’t want to move all that to the iCloud account in Outlook. I just want calendars and contacts to synch seamlessly between iCloud and Outlook. It would seem that between Microsoft and Apple, and all their consumers clamoring for a solution, there would be an easy way to do this. Instead it appears the only solution is to buy a third party software like Code to do the job of synching my personal Outlook folder with my Outlook iCloud folder. Has anyone figured out how to do this type of synch between the Outlook iCloud folder and the Outlook personal file without using additional software/plug-ins? Help!

  7. dale says:

    Have you tried icloud control panel for windows 3.1?

  8. Rob says:

    My wife and I share an icloud account – mainly to sync calendars. We both have separate email and contact lists. In MobileMe and iCloud 1 you could choose to sync only the calendar and not sync the other items (contacts, tasks, etc). With version 2 and above, the only choice is to sync everything (calendar, email, contacts. From my understanding, that would sync my 200+ emails per day with my wife’s 100 emails per day, and that does not include contacts. Is there a way to use icloud to sync only the calendar and not touch the contacts, tasks, or emails?

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